Jonah Hill's Dating History Has a Long List of Women & Only One Engagement

Jonah Hill's dating history is stacked! The actor has dated in and out of the industry, including some women related to famous individuals and friends that he attended school with. Here is the lowdown on his lengthy list of girlfriends and fiancée.

Jonah Hill has come a long way from being the chubby, curly-haired kid that sold humor for a living. The 39-year-old actor has evolved into a more serious personality and instigated the recession of his media presence.

Jonah has been through many relationships as his evolution as an actor progressed. The "21 Jump Street" star has had nine known partners since 2008 and failed to wed the one he proposed to in 2019.

Jordan Klein

Jonah began dating a young lady named Jordan Klein in 2008. The couple attended the same high school and dated for three years before going their separate ways in 2011. During their committed romance, Jonah said, "I have a pretty serious girlfriend, so I really don't think much about dating anymore."

He became sure about the love between Klein and himself to the point that he ruled out the possibility of them splitting. "I really love her a lot, and there's really nothing she can do to deter me from being with her," he added.

Jordan was undoubtedly in love, though, according to a close source. She would travel and accompany the actor in his ever-moving job. The source revealed that things changed when she became permanently employed, and her inability to "pick up and leave" could have contributed to their split.

In 2013, Jonah and Jordan were reunited, and according to an eyewitness, they shared a passionate kiss outside a Starbucks outlet in North Hollywood. They did not stop at that and continued their fiery exchange of affection in the store. The source shared:

"As soon as they sat down [in Starbucks], they started kissing again. They were so into each other it was like there was nobody else in the store. Actually, I think they forgot where they were; it went on for at least five minutes."

Ali Hoffman

Before Jonah's passionate exchange with Jordan in 2013, he was in a relationship with Ali Hoffman—generous Oscar winner Dustin Hoffman's daughter. Jonah also attended the same school as Ali and knew her family well. Their relationship ended after nine months, potentially cutting deeper as he was her father's close friend.

Jonah once mentioned that he became acquainted with Dustin through his children, with whom he attended college and high school. He added that the "Tootsie" star is one of the mentors who got him to take up acting as a career, and Daily Mail revealed that Dustin got Jonah his first role in "I Heart Huckabees."

Jonah prefers to keep the relationships with his partners private and expressed just that when speaking to Howard Stern. "I'm not gonna talk about relationships. This is crazy," the actor complained, denying to open up about his relationship with Ali. However, he added that she was the most incredible person he knew.

Rita Ora

Jonah was reportedly in a short relationship with British singer Rita Ora in 2012. Before they began dating, Rita was in a relationship with Rob Kardashian.

Still, according to the only Kardashian brother, it all came crashing down when he discovered the singer saw other people behind his back.

He used Twitter to expose their fallout bluntly. "She cheated on me with nearly 20 dudes while we were together. I wonder how many she will sleep with now that we are apart?" he said in a now-deleted tweet.

Alana Haim

In 2014, Jonah dated musician and actress Alana Haim. However, their linkage did not stand the test of time, and they broke up in August of that year. Alana was nominated for a BAFTA and Golden Globe award for her applaudable lead performance in Paul Thomas Anderson's movie "Licorice Pizza."

The actor used a provocatively funny approach to shut down the rumors, saying he is engaged to the rumor spreaders' mothers and not his girlfriend.

Although Alana has received much-deserved praise for her acting, most of her work is music related. She has a series of music videos published on YouTube, including visuals for "Summer Girl," "The Steps," "Lost Track," and the most recent collaboration with Taylor Swift on "Bejeweled."

Isabelle McNally

Jonah found a new love in 2013 when he began dating actress Isabelle McNally. Isabelle is known for featuring in projects such as "Loitering with Intent," starring Jewish actress Natasha Lyonne, and four episodes of "House of Cards," previously starring alleged abuser Kevin Spacey.

Jonah and Isabelle were initially spotted together on September 16, 2013. However, a close source revealed they were months into their relationship then. In December of that year, the couple spent a day out celebrating different things in two separate rooms of Tao in New York City.

In March 2014, the paparazzi spotted them again while Isabelle seemed to be talking to an uninterested Jonah. However, their body language when they were sighted in March displayed a considerable disconnect between the lovers.

Brooke Glazer

In terms of relationships, 2014 was the same as the previous years for Jonah. He began dating nutritionist Brooke Glazer in May of that year, and their relationship continued for just over seven months.

The couple was spotted at a park, looking relatively comfortable with each other, with Brooke licking the actor's shades. The park date occurred a month after their first public sighting.

While fans understood Jonah was in a relationship with Brooke, he introduced a new partner to Leonardo DiCaprio, Camille, without revealing her last name. The change in his relationship going undetected by fans is no surprise, as he usually keeps his love life private.

Gianna Santos

Jonah experienced his first moment of advanced commitment in 2019 when he got engaged to his then-girlfriend, content manager Gianna Santos. The actor's sister Beanie Feldstein spoke to reporters about her excitement at the Gold Meets Golden gathering. She said:

"Oh, my God, I mean, he's my best friend in the world, so I'm always excited for him."

The engagement lasted a year before the "21 Jump Street" star split with his fiancée. A source close to the couple revealed that the spark between Jonah and Gianna began to fade away. At the time, Jonah began to lose weight, slimming down to what he called a snapshot moment of his life.

Sarah Brady

Sarah Brady is a graduate of the University of California who got into a relationship with the "You People" star that became known in September 2021. The Sun revealed that Sarah is a Changing Tides Foundation community engagement leader.

Although he is generally private about his love life, Jonah confirmed their romantic link on Instagram when he shared a photo expressing his appreciation for his new lover with a few lovestruck emojis. However, the movie star removed his account from Instagram last year due to anxiety struggles.

Jonah was rumored to be engaged to Sarah last year, despite his public concealment of their relationship. The actor used a provocatively funny approach to shut down the rumors, saying he is engaged to the rumor spreaders' mothers and not his girlfriend.

Olivia Millar

Without any confirmation about the exact date of Jonah's relationship with Sarah's beginning and end, fans can be sure that it is over as he was seen with his newest and current girlfriend, Olivia Millar. She is the sister of Raychel Roberts, a well-known fashion model.

Jonah was seen chatting up his partner before they headed out on vacation to the outskirts of Santa Barbara in September 2022. The actor wore light blue shorts and a white graphic short-sleeve shirt for the beach.

They were spotted again in January this year, lightly dressed, similar to when they went on the road trip last year. With all of the limitations the actor places on media appearances, his fans can be excited about finally seeing him on the big screen again as he starred in the Netflix comedy, "You People" with the family man, Eddie Murphy.